2-oxymethylcarboxylic acid-benzimidazole-arsonic acids and process of preparing them



Patented July 25 193d KARLSTREITWDLF, OF FRANKFORT-ON-THE-IEATN, ALFREDFEI-IRLE, OF BAD SODEN- ON-TAUNUS, AND WALTER HERRMANN, onraannsoar-onmnnmam, GERMANY,. ASSIGNQRS TO WINTHROP CHEMICALcomrnnazano, or new 3031:, n. Y., A ooR- POE-ACTION OF NEW YOE Ka-oxvmnrnyncnnnoxvmo AcIn-BEnzIMfnAzoLn-Ansomc Acres ND PROCESS on UPREPARING THEM No Drawing. Application and Jam-1 20.1931, Serial rid545,845, and in Germany --:r 1y 22. 1930.

The present invention relates to 2-oXymethylcarboxylicacid-benzimidazole-arsonic acids of the following general formulaAs0(OH)2 o.o.omooon V 7 ,X V p whereinX stands for hydrogen or'alkyl,and to a processof preparing them.

VVe'Jhave found that 2-oxymethylcarboxylic acid-benzimidaz'ole-arsomcacids of the above formula are obtained by causing chloracetic acid toact upon benzlmidazolone-arsonic acids of the following general formulaAsowno,

7 wherein Xstandsfor hydrogen or alkyl. It

has beenfound' to be advantageous to carry out the reaction by heatingthe components in presence of a diluent, preferably in an "1 aqueoussolution and in the presence of alkali. From the solution. the newcompounds can be separated by the addition of mineral acid, e. g. ofhydrochloric acid.

The new compounds which are water-soluble are valuable therapeutics andmay also be used as intermediates for preparing other new therapeutics.V

The following examples serveto illustrate the invention, but they arenot intended to '1 limit it thereto.

(1) 90 grams of l-methylbenzimidazolone-S-arsonic acid are dissolved in200 cc. of

" ii introduced into this solution. After boiling for 1 hours in areflux apparatus, another 32 grams of chl'oracetic acid and 58 cc. ofcaustic sodasolution (40 Be'.) are added and the whole is boiled foranother hour. It

is then cooled, neutralized with concentrated hydrochloric acid untilthere is a feebly alkaline reaction to turmeric and filtered. The

l-methyl-Q-oxyacetic acid-benzimidazole a. arsonic acid is separatedfrom the filtrate by means of concentrated hydrochloric acid. The acidis recrystallized from wjater(1-: 6).

The yield of recrystallized acid amounts to It meltsat 808 C. withdecom- 16 grams of chloracetic acid are added thereto and the whole isboiled for 1 hours in a reflux apparatus. Another 16 grams'ofchloracetic acid and 29. cc. of caustic soda solution are added and thewholeis boiled for another hourg It is then cooled and acidified. Theunaltered parent material which has separated is removed by filtering Vby suction and the arsonic acid present in the filtrate is separated inthe form of its v arseno compound by means ofhypophosphorous acid. Thearseno compound which has been washed is dispersed in a small quantityof water and dissolved by addition of ammo: nia. Thissolution isl,oxidized in known manner and the Q-oXyaceticacid-benzimidazole-V5-arsonic acid f is then separated by means ofhydrochloric acid. It is a white powder soluble in water. composes atabout 275 C. with decomposi tion after previously sintering.

.,We claim: 1

On heating it de-- 1. The process which comprises causing chloraceticacid to act upon a compound of the following general formula a ororoz Iwherein X stands for hydrogen or alkyl.

2. The process which comprises heating chloracetic acid with the aqueoussolution of a compound of'the following formula wherein X stands forhydrogen or methyl.

3. The process which comprises heating chloracetic acid with theaqueous. solution of a'colnpound of the following general formulawherein Xstands for hydrogen or methyl, in the presence of alkali. l

4. The process which comprises heating chloracetic acid with the aqueoussolution of a compoundofthefollowing general formula wherein X standsfor hydrogen or methyl,

in the presence of caustic soda'solution, and

separating the compound thus' obtained by" the addition of hydrochloricacid.

7 5. The compounds of the following gen: eral formula wherein Xstandsforhydi'oxy or alkyl, being valuable therapeutics,

6. The compounds of the following general formula #aoornooOn wherein oneY stands for AsO(OH) the other Y for hydrogen and X stands for hydrogenor methyl, being valuable therapeutics.

7. The compound of the following formula Y NH : wherein one Y stands forAs'O(OI-I) the other Y for hydrogen, being a white powder soluble inwater, decomposing at about 275 C. after previous sintering, being avaluable therapeutic. i

8.The compound of the following formula 1',

